Dimethylformamide → Ethyl 7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (100 mg), 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (50 mg), potassium carbonate (83 mg) and N,N-dimethylformamide (20 mL) was stirred at 50° C. for 3 hr. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column to chromatography (ethyl acetate:hexane=60:40 to 100:0, volume ratio) to give the title compound (72 mg, yield 57%) as a white solid. The white solid was recrystallized from ethyl acetate-hexane to give colorless crystals. melting point 91-92° C.

Provenance & Evidence